N-Isopropylacrylamide
[CAS# 2210-25-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-Isopropylacrylamide
• Molecular Formula: C₆H₁₁NO
• Molecular Weight: 113.16
• CAS Registry Number: 2210-25-5
• EC Number: 218-638-5
• SMILES: CC(C)NC(=O)C=C

Properties

• Density: 0.9±0.1 g/cm³, Calc.^*
• Melting point: 60-63 ºC (Expl.)
• Index of Refraction: 1.428, Calc.^*
• Boiling Point: 225.1±13.0 ºC (760 mmHg), Calc.^*, 89-92 ºC(2 mmHg) (Expl.)
• Flash Point: 119.7±4.8 ºC, Calc.^*

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H302-H318-H319
• Precautionary Statements: P264-P264+P265-P270-P273-P280-P301+P317-P305+P351+P338-P305+P354+P338-P317-P330-P337+P317-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

N-Isopropylacrylamide (NIPA) is an organic compound with the molecular formula C6H11NO. It is a colorless liquid that is soluble in water and is primarily used in the synthesis of polymers, particularly for creating temperature-sensitive materials. N-Isopropylacrylamide belongs to a class of compounds known as acrylamides, which are characterized by their ability to form polymers through free-radical polymerization.

The discovery of N-isopropylacrylamide can be traced to the mid-20th century, when researchers were exploring the properties of acrylamide derivatives. NIPA was developed for its unique ability to undergo phase transitions in response to changes in temperature, a property that makes it valuable in a range of applications, including the development of "smart" materials. The compound is known for its lower critical solution temperature (LCST), which is the temperature at which the polymer undergoes a transition from being soluble in water to being insoluble, making it useful for applications that require temperature-responsive behavior.

N-Isopropylacrylamide is most commonly used in the production of hydrogels, which are three-dimensional polymer networks that can absorb and retain large amounts of water. These hydrogels are highly sensitive to temperature and exhibit reversible swelling and deswelling behavior based on changes in temperature. This characteristic makes NIPA-based hydrogels useful in a variety of biomedical and industrial applications, including drug delivery systems, tissue engineering, and wound healing. The ability of NIPA to form temperature-sensitive hydrogels allows for controlled release of drugs or other therapeutic agents in response to external stimuli.

In addition to its biomedical applications, N-Isopropylacrylamide is used in the preparation of water-absorbing materials for applications in agriculture, such as soil conditioners that help retain moisture. The compound is also employed in the creation of coatings, adhesives, and personal care products, where its ability to change physical properties with temperature makes it useful in controlled-release systems.

N-Isopropylacrylamide's polymerization properties are harnessed in the synthesis of copolymers, which are utilized in various industrial applications. For example, NIPA-based copolymers have been studied for use in superabsorbent materials and in the formulation of polymeric surfactants. The compound's versatility as a building block for creating polymers with specific, temperature-sensitive properties contributes to its continued importance in material science and other industrial sectors.

In summary, N-Isopropylacrylamide is a valuable chemical compound primarily used in the synthesis of temperature-sensitive hydrogels and other polymers. Its unique phase-transition properties make it suitable for a wide range of applications in drug delivery, tissue engineering, agriculture, and material science. Its discovery and continued development have led to significant advancements in the fields of biotechnology and polymer chemistry.

References

2004. Temperature-Sensitive Hairy Particles Prepared by Living Radical Graft Polymerization. Langmuir, 20(3).
DOI: 10.1021/la030333k

2024. Versatile programmable somatosensory soft actuators based on highly conductive and robust MXene-integrated hydrogel. Journal of Materials Science, 60(2).
DOI: 10.1007/s10853-024-10425-w

2010. Comb-type grafted poly(N-isopropylacrylamide) gel modified surfaces for rapid detachment of cell sheet. Biomaterials, 31(30).
DOI: 10.1016/j.biomaterials.2010.06.040